Chiral cationic platinum complexes: New catalysts for the activation of carbon-carbon multiple bonds towards nucleophilic enantioselective attack

Current Organic Chemistry

Volumn 14, Issue 12, 2010, Pages 1245-1253

  Toullec, Patrick Y ^a   Michelet, Véronique ^a  

^a PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77954933986     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527210791330431     Document Type: Article

References (84)

1. Fürstner, A.; Davies, P. W. Catalytic carbophilic activation: catalysis byplatinum and gold π-acids. Angew. Chem. Int. Ed. 2007, 46, 3410.
2. Chianese, A. R.; Lee, S. J.; Gagné, M. R. Electrophilic activation of alkenes byplatinum(II): so much more than a slow version of palladium(II). Angew.Chem. Int. Ed. 2007, 46, 4042.
3. Fürstner, A. Gold and platinum catalysis-a convenient tool for generating molecular complexity. Chem. Soc. Rev.2009, 38, 3208.
4. Young, G. B. In Comprehensive Organometallic Chemistry II, (Eds: Abel, E. W.; Stone; Wilkinson, A. G.), Pergamon press: London, 1995, vol.9, 553.
5. Palumbo, R.; De Renzi, A.; Panunzi, A.; Paiaro, G. Addition reactions on coordinated olefinic ligands. I. Reactions of amines with diene complexes of platinum(II) and palladium(II). J. Am. Chem. Soc. 1969, 91, 3874.
6. Panunzi, A.; De Renzi, A.; Palumbo, R.; Paiaro, G. Addition reactions oncoordinated olefinic ligands. II. Reaction between amines and monoolefinscoordinated in cis-dichloro(olefin) (tert-phosphine)platinum(II) complexes. J. Am. Chem. Soc. 1969, 91, 3879.
7. Hahn, C. Enhancing electrophilic alkene activation by increasing the positivenet charge in transition-metal complexes and application in homogeneous catalysis. Chem. Eur. J. 2004, 10, 5888.
8. Eisenstein, O.; Hoffmann, R. Transition-metal complexed olefins: how their reactivity toward a nucleophile relates to their electronic structure. J. Am. Chem. Soc. 1981, 103, 4308.
9. Sasaki, S.; Maruta, K.; Ohkubo, K. Ab initio MO study of palladium-assisted nucleophilic attack on a coordinated olefin: semi quantitative understanding of the reaction and the mechanism of palladium acceleration. Inorg. Chem.1987, 26, 2499.
10. Senn, H. M.; Blöchl, P. E.; Togni, A. Toward an alkene hydroamination catalyst: static and dynamic ab initio DFT studies. J. Am.Chem. Soc. 2000, 122, 4098.
11. Hahn, C.; Cucciolito, M. E.; Vitagliano, A. Coordinated olefins as incipient carbocations: catalytic codimerization of ethylene and internal olefins by adicationic Pt(II) ethylene complex. J. Am. Chem. Soc. 2002, 124, 9038.
12. Hahn, C.; Morvillo, P.; Herdtweck, E.; Vitagliano, A. Coordination ofalkenes at a highly electrophilic site. New dicationic platinum(II) complexes: synthesis, structure, and reactions with nucleophiles. Organometal-lics 2002, 21, 1807.
13. II-mediated po-lycyclization reactions of 1,5- and 1,6-dienes: evidence in support of carbo-cation intermediates. Angew. Chem. Int. Ed. 2004, 43, 3459.
14. Wang, X.; Widenhoefer, R. A. Platinum-catalyzed intermolecular hydroami-nation of unactivated olefins with carboxamides. Organometallics 2004, 23,1649.
15. Bender, C. F.; Widenhoefer, R. A. Platinum-catalyzed intramolecu-lar hydroamination of unactivated olefins with secondary alkylamines. J. Am.Chem. Soc. 2005, 127, 1070.
16. Qian, H.; Widenhoefer, R. A. Platinum-catalyzed intermolecular hydroamination of vinyl arenes with carboxamides. Org. Lett. 2005, 7, 2635.
17. De Renzi, A.; Panunzi, A.; Vitagliano, A. Catalytic dimerisation of olefinsby a cationic platinum(II) complex. Chem. Commun. 1976, 47.
18. Albietz, P. J.; Yang, K.; Lachicotte, R. J.; Eisenberg, R. Cationic unsymmetrical 1,4-diazabutadiene complexes of platinum(II). Organometallics 2000,19, 3543.
19. Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, S. Cationic platinum-complex-catalyzed skeletal reorganization of enynes. Organometallics 2001, 20, 3704.
20. Kerber, W. D.; Koh, J. H.; Gagné, M. R. Platinum(II)-catalyzed 1,6-dienecycloisomerizations: turnover in the absence of β-hydride elimination. Org.Lett. 2004, 6, 3013.
21. Strukul, G.; Michelin, R. A. Catalytic epoxidation of 1-octene with dilutedhydrogen peroxide. On the basic role of hydroxo complexes of platinum(II)and related species. J. Am. Chem. Soc. 1985, 107, 7563.
22. Baccin, C.; Gusso, A.; Pinna, F.; Strukul, G. Platinum-catalyzed oxidations with hydrogen peroxide: the (enantioselective) epoxidation of, α,β-unsaturated ketones. Organometallics 1995, 14, 1161.
23. Zanardo, A.; Michelin, R. A.; Pinna, F.; Strukul, G. Epoxidation of olefins catalyzed by chelating diphosphine-platinum(II) complexes. Ring-size and ring-shape effectson the catalytic activity. Inorg. Chem. 1989, 28, 1648.
24. Pizzo, E.; Sgarbossa, P.; Scarso, A.; Michelin, R. A.; Strukul, G. Second-generation electron-poor platinum(II) complexes as efficient epoxidation catalysts for terminal alkenes with hydrogen peroxide. Organometallics 2006,25, 3056.
25. II complexes. J. Am. Chem. Soc. 2006, 128, 14006.
26. Jacobsen, E. N.; Wu, M. H. In: Comprehensive Asymmetric Catalysis, (Eds.: Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H.), Sprinter: Berlin, 1999,vol. 2, p. 649.
27. Xia, Q.-H.; Ge, H.-Q.; Ye, C.-P.; Liu, Z.-M.; Su, K.-X. Advances in homogeneous and heterogeneous catalytic asymmetric epoxidation. Chem. Rev. 2005, 105, 1603.
28. Colladon, M.; Scarso, A.; Strukul, G. Towards a greener epoxidation method: use of water-surfactant media and catalyst recycling in the platinum-catalyzed asymmetric epoxidation of terminal alkenes with hydrogen peroxide. Adv. Synth. Catal. 2007, 349, 797.
29. II catalysts and hy-drogen peroxide: Supramolecular control of enantioselectivity. Chem. Eur. J.2009, 15, 7930.
30. Belmont, P.; Parker, E. Silver and gold catalysis for cycloisomerizationreactions. Eur. J. Org. Chem. 2009, 35, 6075.
31. Lee, S. I.; Chatani, N. Ca-talytic skeletal reorganization of enynes through electrophilic activation of alkynes: double cleavage of C-C double and triple bonds. Chem. Commun.2009, 371.
32. Jimenez-Nunez, E.; Echavarren, A. M. Gold-catalyzed cycloi-somerizations of enynes: a mechanistic perspective. Chem. Rev. 2008, 108,3326.
33. Michelet, V.; Toullec, P.Y.; Genet, J.-P. Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights. Angew. Chem. Int. Ed. 2008, 45, 7427.
34. Zhang, L.; Sun, J.; Kozmin, S.A. Gold and platinum catalysis of enyne cycloisomerization. Adv. Synth.Catal. 2006, 348, 2271.
35. Fairlamb, I. J. S. Asymmetric cycloisomerizationof 1,6- and 1,7-enynes by transition-metal catalysts. Angew. Chem. Int. Ed. 2004, 43, 1048.
36. Lloyd-Jones, G. C. Mechanistic aspects of transition me-tal catalysed 1,6-diene and 1,6-enyne cycloisomerisation reactions. Org.Biomol. Chem. 2003, 1, 215.
37. Buisine, O.; Aubert, C.; Malacria, M. Thebehavior of 1,n-enynes in the presence of transition metals. Chem. Rev. 2002,102, 813.
38. Charruault, L.; Michelet, V.; Taras, R.; Gladiali, S.; Genêt, J.-P. Functio-nalized carbo- and heterocycles via Pt-catalyzed asymmetric alkoxycyclization of 1,6-enynes. Chem. Commun. 2004, 850.
39. Michelet, V.; Charruault, L.; Gladiali, S.; Genêt, J.-P. Alkoxy- and hydroxycyclization of enynes catalyzed by Pd(II) and Pt(II) catalysts. Pure Appl. Chem. 2006, 78, 397.
40. Gladiali, S.; Dore, A.; Fabbri, D.; De Lucchi, O.; Manassero, M. Novelatropisomeric phosphorus ligands:4,5-dihydro-3H-dinaphtho[2,1-c;1′,2′-e] phosphepine derivatives. Tetrahedron Asymmetry 1994, 5, 511.
41. Junge, K; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Synthesis of new chiral monodentate aminophosphinites and their use in catalytic asymmetric hydrogenations. J. Organomet. Chem. 2003, 675, 91.
42. Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Synthesis of new chiral monodentate phosphines and their use in asymmetric hydrogenation. Tetrahedron Lett. 2002, 43, 4977.
43. Chi, Y.; Zhang, X. Synthesis of novel chiral binaphthyl phosphorus ligands and their applica-tions in Rh-catalyzed asymmetric hydrogenation. Tetrahedron Lett. 2002, 43,4849.
44. For a recent review, see: Gladiali, S. In: "Trivalent PhosphorusCompounds in Asymmetric Catalysis: Synthesis and Applications", Börner,A. Ed., Wiley-VCH, Weinheim, 2008, 177.
45. Nevado, C.; Charruault, L.; Michelet, V.; Nieto-Oberhuber, C.; Muñoz, M. P.; Méndez, M.; Rager, M.-N.; Genêt, J.-P.; Echavarren, A. M. On themechanism of carbohydroxypalladation of enynes. Additional insights on thecyclization of enynes with electrophilic metal complexes. Eur. J. Org. Chem.2003, 706.
46. 2 or other transition metal chlorides: divergent reaction pathways. J. Am. Chem. Soc. 2001,123, 10511 and references cited therein.
47. Chisholm, M. H.; Clark, H. C. Cationic acetylenic platinum(II) compoundsand their derivatives. III. Reactions of platinum(II) stabilized carboniumions. J. Am. Chem. Soc. 1972, 94, 1532.
48. Muñoz, M. P.; Adrio, J.; Carretero, J. C.; Echavarren, A. M. Ligand effectsin gold- and platinum-catalyzed cyclization of enynes: chiral gold complexes for enantioselective alkoxycyclization. Organometallics 2005, 24,1293.
49. I-catalyzed C-C bond formation through a tandem Friedel-Crafts-type addition/carbocyclization reaction. Angew. Chem. Int. Ed. 2006,45, 7427.
50. Toullec, P.Y.; Chao, C.-M.; Chen, Q.; Genêt, J.-P.; Michelet, V. Enantioselec-tive platinum-catalyzed tandem hydroarylation-cycloisomerization of 1,6-enynes. Adv. Synth. Catal. 2008, 250, 2401.
51. Brissy, D.; Skander, M.; Retailleau, P.; Marinetti, A. N-Heterocycliccarbenes in the synthesis of axially chiral square-planar platinum complexes. Organometallics 2007, 26, 5782.
52. Brissy, D.; Skander, M.; Retailleau, P.; Frison, G.; Marinetti, A. Platinum(II) complexes featuring chiral diphosphi-nes and N-heterocyclic carbene ligands: synthesis and evaluation as cycloi-somerization catalysts. Organometallics 2009, 28, 140.
53. Brissy, D.; Skander, M.; Jullien, H.; Retailleau, P.; Marinetti, A. Platinum(II) catalystsfor highly enantioselective 1,6-enyne cycloisomerizations. synthetic, structu-ral, and catalytic studies. Org. Lett. 2009, 11, 2137.
54. Blum, J.; Beer-Kraft, H.; Badrieh, Y. A novel platinum tetrachloride-catalyzed cyclorearrangement of allyl propynyl ethers to 3-oxabicyclo[4.1.0]heptenes. J. Org. Chem. 1995, 60, 5567.
55. Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, K. Construction of novel polycyclic ring systems by transition-metal-catalyzed cycloisomerization ofene ene ynes. interception of a carbenoid intermediate in skeletal reorgani-zation of enynes. J. Am. Chem. Soc. 1998, 120, 9104.
56. 2. J. Am.Chem. Soc. 2000, 122, 6785.
57. Furstner, A.; Stelzer, F.; Szillat, H. Platinum-catalyzed cycloisomerization reactions of enynes. J. Am. Chem. Soc.2001, 123, 11863.
58. Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. Platinum-catalyzed intramolecular alkylation of indoles with unactivated olefins. J. Am. Chem. Soc.2004, 126, 3700.
59. Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. Platinum-catalyzed intramolecular alkylation of indoles with unactivated olefins. J. Am. Chem. Soc. 2004, 126, 10493.
60. Han, X.; Widenhoefer, R. A. Platinum-catalyzed intramolecular asymmetrichydroarylation of unactivated alkenes with indoles. Org. Lett. 2006, 8, 3801.
61. Dicationic platinum complexes of type 35 efficiently catalyze a range ofenantioselective transformations. For selected examples, see
62. Hetero Di-els-Alder cycloaddition: Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. Asymmetric hetero Diels Alder reaction catalyzed by chiralcationic palladium(II) and platinum(II) complexes. J. Org. Chem. 1999, 64,8660.
63. Diels-Alder cycloaddition: Ghosh, A. K.; Matsuda, H. Counterions of BINAP Pt(II) and Pd(II) complexes: novel catalysts for highly enantio-selective Diels Alder reaction. Org. Lett. 1999, 1, 2157.
64. Ene reaction: Koh, J. H.; Larsen, A. O.; Gagné, M. R. Asymmetric Pt(II)-catalyzed enereactions: counterion-dependent additive and diphosphine electronic effects.Org. Lett. 2001, 3, 1233.
65. Prins reaction: Mullen, C. A.; Gagné, M. R. Catalytic asymmetric prins cyclizations: cation generation and trapping with (BINAP)Pt dications. Org. Lett. 2006, 8, 665.
66. 1-coordination of the oxygen lone pair of thesubstrate, see
67. Pignat, K.; Vallotto, J.; Pinna, F.; Strukul, G. Cationic com-plexes of palladium(II) and platinum(II) as Lewis acid catalysts for the Diels Alder reaction. Organometallics 2000, 19, 5160.
68. Huang, H.; Peters, R. A Highly strained planar-chiral platinacycle for catalytic activation of internal olefins in the Friedel-Crafts alkylation of indoles. Angew. Chem. Int. Ed. 2009, 48, 604.
69. Jautze, S.; Seiler, P.; Peters, R. Macrocyclic ferrocenyl-bisimidazolinePalladacycle dimers as highly active and enantioselective catalysts for the Aza-Claisen rearrangement of Z-configured N-para-methoxyphenyl trifluo-roacetimidates. Angew. Chem. Int. Ed. 2007, 46, 1260.
70. Jautze, S.; Seiler, P.; Peters, R. Synthesis of nearly enantiopure allylic amines by Aza-Claisen rearrangement of Z-configured allylic trifluoroacetimidates catalyzed by highly active ferrocenylbispalladacycles. Chem. Eur. J. 2008, 14, 1430.
71. Jautze, S.; Peters, R. Enantioselective bimetallic catalysis of Michael additions forming quaternary stereocenters. Angew. Chem. Int. Ed. 2008, 47, 9284.
72. Kerber, W. D.; Gagné, M. R. Cycloisomerization of dienes with carbophilic Lewis acids: mimicking terpene biosynthesis with Pt(II) catalysts. Org. Lett.2005, 7, 3379.
73. Feducia, J. A.; Campbell, A. N.; Doherty, M. Q.; Gagné, M. R. Modularcatalysts for diene cycloisomerization: rapid and enantioselective variants for bicyclopropane synthesis. J. Am. Chem. Soc. 2006, 128, 13290.
74. To the best of our knowledge, very few reports of gold (I)-catalyzed highlyenantioselective transformations have appeared in the literature, see
75. Ito, Y.; Sawamura, M.; Hayashi, T. Catalytic asymmetric aldol reaction: reactionof aldehydes with isocyanoacetate catalyzed by a chiral ferrocenylphosphine-gold(I) complex. J. Am. Chem. Soc. 1986, 108, 6405.
76. González-Arellano, C.; Corma, A.; Iglesias, M.; Sánchez, F. Chem. Commun. 2005, 3451.
77. Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. Gold(I)-catalyzed ste-reoselective olefin cyclopropanation. J. Am. Chem. Soc. 2005, 127, 18002.
78. Chao, C.-M.; Genin, E.; Toullec, P.Y.; Genêt, J.-P.; Michelet, V. Towards asymmetric Au-catalyzed hydroxy- and alkoxycyclization of 1,6-enynes. J.Organomet. Chem. 2009, 694, 538.
79. Chao, C.-M.; Vitale, M. R.; Toullec, P.Y.; Genêt, J.-P.; Michelet, V. Asymmetric gold-catalyzed hydroarylation/cyclization reactions. Chem. Eur. J. 2009, 15, 1319.
80. Watson, I. D. G.;Ritter, S.; Toste, F. D. Asymmetric synthesis of medium-sized rings by in-tramolecular Au(I)-catalyzed cyclopropanation. J. Am. Chem. Soc. 2009,131, 2056.
81. Chao, C.-M.; Beltrami, D.; Toullec, P. Y.; Michelet, V. Asymme-tric Au(I)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cy-cloisomerization process of 1,6-enynes. Chem. Commun. 2009, 6988.
82. For a discussion regarding the difficulties associated with the development ofgold-catalyzed asymmetric transformations, see for example: Corkey, B. K.; Toste, F. D. Catalytic enantioselective coniaene reaction. J. Am. Chem. Soc.2005, 127, 17168.
83. Bongers, N.; Krause, N. Golden opportunities instereoselective catalysis. Angew. Chem. Int. Ed. 2008, 47, 2178 and references cited therein.
84. Widenhoefer, R. A. Recent developments in enantio-selective gold(I) catalysis. Chem. Eur. J. 2008, 5382.